Department of Organic Chemistry. Faculty of Chemistry, Complutense University of Madrid, Ciudad Universitaria, 28040, Madrid, Spain.
Chempluschem. 2020 Oct;85(10):2252-2271. doi: 10.1002/cplu.202000448.
The 1,3-dipolar cycloaddition reactions (DCs) of nitrile oxides (NOs) to alkenes and alkynes are useful methods for the synthesis of 2-isoxazolines and isoxazoles respectively, which are important classes of heterocyclic compounds in organic and medicinal chemistry. Most of these reactions are carried out in organic solvents and under thermal activation. Nevertheless the use of supercritical carbon dioxide (scCO ) and ionic liquids (Ils) as alternative solvents and the application of microwave (MW) and ultrasound (US) as alternative activation procedures have evident advantages from the "Green Chemistry" point of view. The critical discussion on the applications of these "unconventional" activation methods and reaction conditions in the 1,3-DCs of NOs is the objective of the present Review.
1,3-偶极环加成反应(DCs)的腈氧化物(NOs)的烯烃和炔烃是分别用于合成2-异恶唑啉和异恶唑的有用方法,它们是有机和药物化学中重要的杂环化合物类别。这些反应大多数是在有机溶剂中并在热激活下进行的。然而,超临界二氧化碳(scCO2)和离子液体(Ils)作为替代溶剂的使用以及微波(MW)和超声(US)作为替代激活程序的应用,从“绿色化学”的角度来看具有明显的优势。本综述的目的是对这些“非常规”激活方法和反应条件在NOs的 1,3-DCs 中的应用进行批判性讨论。